ECMDB: lipoate (ECMDB23028) (M2MDB003418)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (254)

Record Information

Version

2.0

Creation Date

2012-10-10 12:13:10 -0600

Update Date

2015-08-05 16:22:03 -0600

Secondary Accession Numbers

ECMDB23028

Identification

Name:

lipoate

Description

A thia fatty acid anion that is the conjugate base of lipoic acid; major species at pH 7.3.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

1,2-Dithiolane-3-pentanoate
1,2-Dithiolane-3-pentanoic acid
1,2-Dithiolane-3-valerate
1,2-Dithiolane-3-valeric acid
5-(1,2-Dithiolan-3-yl)valerate
5-(1,2-Dithiolan-3-yl)valeric acid
5-(Dithiolan-3-yl)valerate
5-(Dithiolan-3-yl)valeric acid
5-[3-(1,2-Dithiolanyl)]pentanoate
5-[3-(1,2-Dithiolanyl)]pentanoic acid
6,8-Thioctate
6,8-Thioctic acid
6,8-Thiotate
6,8-Thiotic acid
6-Thioctate
6-Thioctic acid
6-Thiotate
6-Thiotic acid
a-Lipoate
a-Lipoic acid
a-Liponsaeure
Acetate-replacing factor
Acetic acid-replacing factor
alpha-Lipoate
alpha-Lipoic acid
alpha-Liponsaeure
Biletan
Lipoic acid
Liponate
Liponic acid
Thioctansaeure
Thioctate
Thioctic acid
Thioctsaeure
Thioktsaeure
α-Lipoate
α-Lipoic acid
α-Liponsaeure

Chemical Formula:

C₈H₁₄O₂S₂

Weight:

Average: 206.326
Monoisotopic: 206.043521072

InChI Key:

AGBQKNBQESQNJD-UHFFFAOYSA-N

InChI:

InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)

CAS number:

62-46-4

IUPAC Name:

5-(1,2-dithiolan-3-yl)pentanoic acid

Traditional IUPAC Name:

6,8-thioctic acid

SMILES:

OC(=O)CCCCC1CCSS1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithiolanes

Sub Class

Lipoic acids and derivatives

Direct Parent

Lipoic acids and derivatives

Alternative Parents

Substituents

Lipoic_acid_derivative
Medium-chain fatty acid
Heterocyclic fatty acid
Thia fatty acid
Fatty acyl
Fatty acid
1,2-dithiolane
Organic disulfide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dithiolanes (CHEBI:16494 )
thia fatty acid (CHEBI:16494 )
heterocyclic fatty acid (CHEBI:16494 )
Prosthetic group [Fig] (C00725 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
Water Solubility:	2.24e-01 g/l	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.75	ALOGPS
logP	2.11	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	54.37 m³·mol⁻¹	ChemAxon
Polarizability	22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Adenosine triphosphate + lipoate > Pyrophosphate + Lipoyl-AMP
Adenosine triphosphate + lipoate + Lipoyl-AMP + Apoprotein <> Pyrophosphate + Protein N6-(lipoyl)lysine + Adenosine monophosphate
lipoate + Adenosine triphosphate > Lipoyl-AMP + Pyrophosphate + Lipoyl-AMP

SMPDB Pathways:

Lipoic acid metabolism

PW000770

KEGG Pathways:

Lipoic acid metabolism ec00785
Metabolic pathways eco01100

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4900000000-59fc063b5aa5a8b5db19	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-50da42c94591e9a60c0f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-1346e3a528dca0514cf7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-03di-9000000000-420a38a26d85b4091edb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-03di-9000000000-24b63eebe2fd067ce4b8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0229-6900000000-44bcc93e18aeabd9ee16	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03k9-9600000000-4f680dfeae7fa1ece57a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-03di-9000000000-6f0b91016a33e202e49b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-03di-9000000000-e3d4a7fe022cf20db036	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0920000000-cf913d1d1afc04e5450c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bti-5910000000-294c510229247ef63f20	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-9600000000-f8f54eb79c5d4d5bef48	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0920000000-5a823a30dd1fb434e5b1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kmu-1910000000-6f491a68afd82922e71b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9200000000-330e4766f82ed571497b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0970000000-0ae5b11a032d11c1ba6d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-decf255617c1bbd69bfb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-6900000000-eb58a3d8135ba85d4283	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0190000000-014d2ea36cfae0726a9e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9500000000-9bbbd7b252fb9a0b438d	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16494
HMDB ID	HMDB14312
Pubchem Compound ID	864
Kegg ID	C00725
ChemSpider ID	841
Wikipedia	Lipoic_Acid
BioCyc ID	Not Available

Enzymes

Protein Details

1. Lipoate-protein ligase A

General function:: Involved in catalytic activity
Specific function:: Catalyzes both the ATP-dependent activation of exogenously supplied lipoate to lipoyl-AMP and the transfer of the activated lipoyl onto the lipoyl domains of lipoate-dependent enzymes. Is also able to catalyze very poorly the transfer of lipoyl and octanoyl moiety from their acyl carrier protein
Gene Name:: lplA
Uniprot ID:: P32099
Molecular weight:: 37926

Reactions

ATP + lipoate = diphosphate + lipoyl-AMP.
Lipoyl-AMP + protein = protein N(6)-(lipoyl)lysine + AMP.

lipoate (ECMDB23028) (M2MDB003418)

Structure for #<Compound:0xa5d2a4c4>

Enzymes

Reactions